Potassium Carbonate → 2-bromo-1-(5-fluoro-3-methoxy-2-nitrophenyl)-4-methyl-1H-imidazole

HRID 254321Notes

Reaction equation

HRID 254321 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[N+:11]([O-:13])=[O:12].[Br:14][C:15]1[NH:16][CH:17]=[C:18]([CH3:20])[N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.ClCCl>[Br:14][C:15]1[N:16]([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([O:9][CH3:10])[C:3]=2[N+:11]([O-:13])=[O:12])[CH:17]=[C:18]([CH3:20])[N:19]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 103301291,5-Difluoro-3-methoxy-2-nitrobenzeneHCID 178430836HCID 178430836, compound

Product 1

HCID 577324692-bromo-1-(5-fluoro-3-methoxy-2-nitrophenyl)-4-methyl-1H-imidazoleYield 31%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,5-difluoro-3-methoxy-2-nitrobenzene (9 g, 47.6 mmol), 2-bromo-4-methylimidazole (7.7 g, 47.6 mmol) and potassium carbonate (14.5 g, 104.7 mmol) in 240 mL DMF was stirred at room temperature overnight. The majority of solvent was removed by rotavap and the residue was diluted with ethyl acetate and washed with water. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with water, brined, dried over magnesium sulfate. Condensation and purification using 5-10% ethyl acetate in dichloromethane as eluent provided 4.8 g (31% yield) of 2-bromo-1-(5-fluoro-3-methoxy-2-nitrophenyl)-4-methyl-1H-imidazole as a yellow solid. 1H NMR (400 MHz, DMSO) δ ppm 7.60 (dd, 1H), 7.38 (dd, 1H), 7.21 (s, 1H), 3.98 (s, 3H), 2.09 (s, 3H). EIMS 330.0 [M+H]+.

Workup

  1. customThe majority of solvent was removed by rotavap
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe combined organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customCondensation and purification

Sources & evidence

ORD record
ord-c9dc8fd2457f4ba9b401cfa23d75aca3
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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